Reader's Dilemma: My Crush Had a Fling With My Roommate. And I Still Want to Date Him!

Generally speaking, it's not the best idea to date a best friend's ex. But when the two people in question are your roommate and a guy friend whom you've had a crush on and they didn't really date, things get kind of dicey.

Generally speaking, it's not the best idea to date a best friend's ex. But when the two people in question are your roommate and a guy friend whom you've had a crush on and they didn't really date, things get kind of dicey.

A sweet reader recently sent us this email:

Help! I'm in a situation and I'm not sure what to do about it. I have a guy friend that I'm very close with, we've always had chemistry together, but when we met and until recently I was in a relationship with someone else. Despite that there's always been a little something there. Now that I am single we've been flirting a lot more and both want to be together. The only problem is that he was talking to my roommate for a month or so, which has since also ended. Now I'm not sure what to do. I've been interested in him for a while but now that my roommate was interested in him the situation is complicated. What should I do?!

And here's what I think:

Thank you for reaching out! And sorry to hear that you're in the middle of what sounds like a romantic comedy.

Before you decide to move forward, I think it's important to consider what kind of relationships you want to have with both your roommate and your friend. Is the roommate a good friend? How do you think she'd feel if you dated this guy? Did she know you had feelings for him all this time? Could you see yourself just being friends with this guy? Or are you two only interested in having a romantic relationship now?

Next, what kind of interaction did your roommate and friend have when they were "talking?" If it was just silly flirting, I don't think it's too big of a deal if you and your guy pursue something. But if it was something deeper, perhaps they went on a few dates or even slept together, how does that make you feel? If you're not bothered by it, go for it. But if it rubs you the wrong way, or you don't think it's something you can get over, starting a relationship with this fellow might be a bit difficult.

Lastly, how (and why) did things end for these two? Did they just not have chemistry and things fizzled? If there was some big drama involved, I'd think twice about getting involved. It might be best to let the situation cool down before jumping in.

What do you think our reader should do? Have you ever been in a similar situation? Could you date a roommate's ex? Would you feel weird if your roommate dated one of your crushes?